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For years I treated date night dressing as a waste of effort, on the basis that if someone likes you after three dates they're not going to bin you off over a shirt. What changed my mind was turning up to a July dinner in the wrong fabric, sweating through a conversation about holiday plans, and realising the problem wasn't nerves, it was that I'd dressed for an office, not an evening.
Once I started treating it properly, the rest of an ordinary wardrobe did most of the heavy lifting. A linen or linen blend shirt worn open over a plain t-shirt covers most restaurants and most bars without trying too hard. Lighter trousers, chino or a soft cotton, do the job better than jeans once the temperature climbs, mainly because they don't cling by the second course. Loafers or clean trainers both work, it depends on the venue rather than any rule, and a jacket is worth carrying even if it spends the night over the back of a chair, because a lot of places still cool off fast once the sun's gone.
In the shop, the checks are quick ones. Hold the shirt up to the light, if you can see your hand through it clearly it'll crease into a mess within the hour and show every bit of sweat, which is not the look you want across a small table. Pinch the trouser fabric between two fingers, if it feels stiff or papery it'll bag at the knee by the main course. Check the shirt collar sits flat against your neck without gaping, and roll the sleeves up to see if they stay rolled or spring straight back down, because nobody wants to be fighting their own cuffs mid conversation. For jackets, undo the top button and sit down in it if there's a chair nearby, if it pulls across the chest or rides up at the back, leave it.
If you're starting from nothing, go for one linen shirt in a pale colour, one pair of lighter trousers in a neutral shade, and shoes you already know are comfortable for standing around in. Build out from there once you know what actually gets worn twice a week rather than once a summer.
Linen softens properly after a few washes and starts moving the way it's meant to from the start. Lighter trousers fade slightly with sun and washing, which looks better than new, not worse. The whole lot gets easier to wear in, and that's really the point of it.
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